Ammonia and its derivatives are highly useful basic compounds which have many known uses. The family of ammonia compounds, for example, amines, amides, ureas, hydrazines, hydrazides, hydrazones, amidrazones, semicarbazides and semicarbazones, are useful in a variety of organic syntheses. The preparation of such basic ammonia compounds and their derivatives, however, is often costly and difficult, requiring many steps (See, e.g., U.S. Pat. No. 3,956,366).
Among these ammonia derivatives, hydrazide and hydrazine compounds are particularly useful as reducing agents in organic syntheses. However, the high cost of producing reagent quality hydrazides and hydrazines has reduced their practical utility in organic synthesis, such as in the production of acylated hydrazides or hydrazines. Such compounds have demonstrated useful insecticidal activity (See, e.g., U.S. Pat. No. 4,985,461, Japanese patent applications JP-091048 and JP-020216, and German patent application DE 3228631).
Efforts have been made to prepare such useful hydrazides, hydrazines, and substituted derivatives thereof, at low cost and in high yield without much success (see, e.g., U.S. Pat. Nos. 4,310,696, 4,435,600 and 4,954,655). The processes referred to in the above-listed patents are expensive, time consuming, and labor intensive.
There remains a need for a simple, low cost method to prepare hydrazide or hydrazine compounds so that their beneficial properties can be made readily available to the public.
It is therefore an object of this invention to provide a process for the preparation of hydrazide or hydrazine compounds from readily available urea compounds.
Yet another object of the invention is to provide a more efficient process for preparation of substituted hydrazide or hydrazine compounds.
Another object of the invention is to provide a controlled method for the monoacylation and diacylation of urea compounds.
These and other objects of the invention will become apparent in the course of the detailed description of the invention which follows.